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How To Destroy A Tech Startup In Three Easy Steps
Insane ambition. Insane deadlines. Insane leadership. A software death march. A true story. It began with an ingenious to use the software techniques known as Natural Language Processing to allow people to interact with databases by writing ordinary English sentences. This was a multi-billion dollar idea that could have transformed the way people gathered and used information. However, the venture had inexperienced leadership. They burned through their $1.3 million seed money. As their resources dwindled, their confidence transformed into doubt, which was aggravated by edicts from the Board Of Directors ordering sudden changes that effectively threw away weeks' worth of work. Working from the company emails and Slack messages, the authors re-create the actual day to day battles that gave rise to the early optimism, and also show the moment when euphoria transformed into panic. Here then, is a cautionary tale, a warning about tendencies that everyone joining a startup should be on guard against.
225 pages, Kindle Edition
Published October 31, 2017
103 people are currently reading
181 people want to read
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Displaying 1 - 23 of 23 reviews
April 12, 2021
Everybody wants to ride a unicorn, take their IPO to the moon, party on the Playa with Elon, and generally be lauded as a genius. But the fact is, most startups fail. And while studies of some notably fraudulent failures have had a great deal of success: Theranos, WeWork, FyreFest, most companies fail for more mundane reasons. In the summer of 2015, Krubner was a software developer working at a startup in New York. The startup had a clever idea to allow salespeople to interface with their Customer Relationship Management (CRM) database with a slick smartphone app using natural language processing (NLP) instead of doing incredibly tedious data entry. Krubner expected, well, a job that made sense. What he got was a six month journey into a vortex of deception and psychological abuse. Most of us have been in situations that were kind of messed up. Krubner took notes, and then he took the gloriously self-destructive step of publishing this book. The names have been changed to protect the guilty, except for his own.
I actually know a little bit about NLP, and while getting "okay" results out of NLP is pretty doable, getting perfect results is incredibly hard. Like, "the best minds Google can hire with all the cloud compute they want" hard. Listening to the business statement of the startup makes me want to reach for my gun. Hearing that anybody would rely on this for major deals makes me sure to save the last bullet for myself.
Krubner was hired for a pretty standard dev role, plugging an iphone app in development into an NLP model and then Saleforce's CRM database. The hard bit was the NLP model, and a quote-unquote "brilliant data scientist" Sital had been hired to build it. But Sital spent all day watching weight lifting videos on Youtube and had mediocre coding abilities. Two of the 'cofounders', including the Chief Technology Officer, vanished to Silicon Valley internships.
Krubner put in long hours, but bugs derailed demos and core pieces of the software simple didn't work. And this is where the pyschodrama began to unravel. The CEO was a young college grad named John, and his typo-ridden messages became increasingly erratic under pressure from the board of directors. It seemed that John was just the front for the most active member of the board, a man by the name of Milburn. Milburn was a middle-aged salesman who had taught himself enough Visual Basic in the 90s to claim to be a programmer. He'd had an idea, and picked the malleable John, the son of a friend and former intern, to implement it. As John failed, because the task was beyond the team's capabilities, Milburn became increasingly involved and manipulative, finally confronting Krubner in a barrage of insults and accusations that Krubner was sabotaging the company. That was the end for their relationship.
I've searched some other reviews of the book, and an older essay that had some of the same story. There is an air of incredulity from some of the commenters. There's no way Sital could be so incompetent, Milburn so Machiavellian, or Krubner such a stereotype of the stolid software engineer. I would sincerely like to have these people's blessedly competent lives, because I'm at a boring suit and tie company with good processes and stable cashflow, and I've seen everything he written about here in software development. And as for why he stuck with it. Well, apparently the incubator was really fun, and it beat the hell out of his previous job as a developer for a serially failed founder.
This little startup was likely doomed from the start, but some advice generalizes nicely. A startup has to be a radically transparent learning organization or it is dead. Lies and deception are fatal. A team is only as strong as its weakest member, and weak links have to be cut mercilessly. And the real leader has to be involved and accountable to the process, having enough strength of will to bring something new into the world while not being so caught up in ego that they're unable to admit mistakes.
And Lawrence, if you ever decide to do a PhD, please take some good notes.
I actually know a little bit about NLP, and while getting "okay" results out of NLP is pretty doable, getting perfect results is incredibly hard. Like, "the best minds Google can hire with all the cloud compute they want" hard. Listening to the business statement of the startup makes me want to reach for my gun. Hearing that anybody would rely on this for major deals makes me sure to save the last bullet for myself.
Krubner was hired for a pretty standard dev role, plugging an iphone app in development into an NLP model and then Saleforce's CRM database. The hard bit was the NLP model, and a quote-unquote "brilliant data scientist" Sital had been hired to build it. But Sital spent all day watching weight lifting videos on Youtube and had mediocre coding abilities. Two of the 'cofounders', including the Chief Technology Officer, vanished to Silicon Valley internships.
Krubner put in long hours, but bugs derailed demos and core pieces of the software simple didn't work. And this is where the pyschodrama began to unravel. The CEO was a young college grad named John, and his typo-ridden messages became increasingly erratic under pressure from the board of directors. It seemed that John was just the front for the most active member of the board, a man by the name of Milburn. Milburn was a middle-aged salesman who had taught himself enough Visual Basic in the 90s to claim to be a programmer. He'd had an idea, and picked the malleable John, the son of a friend and former intern, to implement it. As John failed, because the task was beyond the team's capabilities, Milburn became increasingly involved and manipulative, finally confronting Krubner in a barrage of insults and accusations that Krubner was sabotaging the company. That was the end for their relationship.
I've searched some other reviews of the book, and an older essay that had some of the same story. There is an air of incredulity from some of the commenters. There's no way Sital could be so incompetent, Milburn so Machiavellian, or Krubner such a stereotype of the stolid software engineer. I would sincerely like to have these people's blessedly competent lives, because I'm at a boring suit and tie company with good processes and stable cashflow, and I've seen everything he written about here in software development. And as for why he stuck with it. Well, apparently the incubator was really fun, and it beat the hell out of his previous job as a developer for a serially failed founder.
This little startup was likely doomed from the start, but some advice generalizes nicely. A startup has to be a radically transparent learning organization or it is dead. Lies and deception are fatal. A team is only as strong as its weakest member, and weak links have to be cut mercilessly. And the real leader has to be involved and accountable to the process, having enough strength of will to bring something new into the world while not being so caught up in ego that they're unable to admit mistakes.
And Lawrence, if you ever decide to do a PhD, please take some good notes.
September 4, 2020
A somewhat funny story of a failed startup. Claims to be a true story taken from the life of the main author. I hear it resonates more with employees than with founders. At 172 pages, it was a quick read. When it first came to my attention, the startup was going to be about using NLP to talk to databases. I imagined NLP instead of SQL. Could be entertaining. A shorter, lighter fare than The Phoenix Project, maybe?
For the most part, the narrator simply recounts events as he saw them. His perspective is that of a truthful and reliable dev guy. He's trying his best to convey complex technical tasks as accurately as he can, to make sure everyone is on the same page. He paints the biz guy as shifty and somewhat out of touch, constantly ignoring the narrator in favor of whatever make him look best. It is only towards the end of the book, when the real power behind the company is revealed and they try to use a long list of psychological tricks to manipulate the narrator, that the book become more introspective and analytical. At last, the narrator pauses to reflect on what is happening and lets us in on his deeper thoughts. It was interesting to see his reflections regarding the darker, more aggressive side of sales tactics and the various attempts at psychological manipulation (i.e., gaslighting).
There is bound to be some bias. The narrator has all the good, honest qualities and his antagonist displays all the negative traits. Is the narrator reliable? Was the business guy really so much of a sociopath? Did development really proceed at such a slow pace?
I related to the context of the book. A tech startup, a small team of people trying to get the application running, technologies very close to what I use in my daily professional life (Unix pipes, websockets, Redis, Twilio, finite state machines). I also dig the Manhattan geography. It was satisfying to imagine myself as the protagonist and see the business people as the enemies. But real life is much more nuanced. The characters were almost caricatures.
While there are many challenges in building services and integrating with APIs like Salesforce and doing NLP, I was underwhelmed by what the team was able to achieve in the span of six months. If the narrator really has 10-15 years of experience in startups, he should have stepped in immediately to get things under control instead of waiting for someone else. On a six person team, there is no room for hierarchy and passing the buck around. If you see a problem, you fix the problem. There is no one else to do it for you.
I have had run-ins with people who thought they could parley themselves into alternate realities. They exist on the dev side and on the biz side. Two quotes summed up perfectly how I tend to interact with such people:
and
As a quick note, throughout the book, whenever I read "Milburn", I kept imagining the character of Milton from the movie "Office Space". In the last section of the book, "Responses to Others", the author actually refers to Milburn as "Milton".
For the most part, the narrator simply recounts events as he saw them. His perspective is that of a truthful and reliable dev guy. He's trying his best to convey complex technical tasks as accurately as he can, to make sure everyone is on the same page. He paints the biz guy as shifty and somewhat out of touch, constantly ignoring the narrator in favor of whatever make him look best. It is only towards the end of the book, when the real power behind the company is revealed and they try to use a long list of psychological tricks to manipulate the narrator, that the book become more introspective and analytical. At last, the narrator pauses to reflect on what is happening and lets us in on his deeper thoughts. It was interesting to see his reflections regarding the darker, more aggressive side of sales tactics and the various attempts at psychological manipulation (i.e., gaslighting).
There is bound to be some bias. The narrator has all the good, honest qualities and his antagonist displays all the negative traits. Is the narrator reliable? Was the business guy really so much of a sociopath? Did development really proceed at such a slow pace?
I related to the context of the book. A tech startup, a small team of people trying to get the application running, technologies very close to what I use in my daily professional life (Unix pipes, websockets, Redis, Twilio, finite state machines). I also dig the Manhattan geography. It was satisfying to imagine myself as the protagonist and see the business people as the enemies. But real life is much more nuanced. The characters were almost caricatures.
While there are many challenges in building services and integrating with APIs like Salesforce and doing NLP, I was underwhelmed by what the team was able to achieve in the span of six months. If the narrator really has 10-15 years of experience in startups, he should have stepped in immediately to get things under control instead of waiting for someone else. On a six person team, there is no room for hierarchy and passing the buck around. If you see a problem, you fix the problem. There is no one else to do it for you.
I have had run-ins with people who thought they could parley themselves into alternate realities. They exist on the dev side and on the biz side. Two quotes summed up perfectly how I tend to interact with such people:
it would be a mistake to respond as if we were having a good faith conversation, eagerly trying to discover the real facts of the situation (p. 130)
and
the thing about reality is that it always wins in the end. (p. 143)
As a quick note, throughout the book, whenever I read "Milburn", I kept imagining the character of Milton from the movie "Office Space". In the last section of the book, "Responses to Others", the author actually refers to Milburn as "Milton".
December 25, 2017
i read this recent book and liked it. it rang very true, i founded and was ceo of 2 startups - franz.com and pandorabots.com . most of the patterns for failure the author identified i've personally encountered. this book is worth reading and studying. -fritz kunze (fkunze@gmail.com)
April 12, 2021
Certainly an interesting view from the inside of a startup
February 26, 2020
If you enjoyed Soul of a New Machine by Tracy Kidder and the TV show Halt and Catch Fire, you will enjoy Lawrence Krubner very funny "work of fiction" in which he deals with bright eyed young folk who have come up with a creative idea and decide to grow a startup. Programmers and computer geeks will cringe in recognition at the horrors and madness that take place while trying to create a billion dollar earning-company. I lived through it in 2000 during the first dot com explosion. I laughed and cried as I relived my days as the head writer and editor of a new startup while sitting with the programmers. Learned some great new swear words and a little HTML.
May 8, 2020
Fascinating details of pathological behaviour at work
I don’t know why the author persisted in working at such a bad company but I’m glad he did as he spelled out the consequences in tedious detail. It is tempting to read it and think “there but for the grade of God go I” but I found my self reflecting on recent conversations and thinking “am I doing what he is describing”? It was useful to reconstruct and reinterpret daily behaviour. We are all operating in the fog of war with incomplete information and immature abilities in insufficient time. So we make mistakes and move on hoping to move up.
I wish the author happiness in his current job.
I don’t know why the author persisted in working at such a bad company but I’m glad he did as he spelled out the consequences in tedious detail. It is tempting to read it and think “there but for the grade of God go I” but I found my self reflecting on recent conversations and thinking “am I doing what he is describing”? It was useful to reconstruct and reinterpret daily behaviour. We are all operating in the fog of war with incomplete information and immature abilities in insufficient time. So we make mistakes and move on hoping to move up.
I wish the author happiness in his current job.
July 15, 2020
Loved how relatable it was. It really made the interesting because I could see myself in the same situations the author was going through.
I also loved the structure of the book. No traditional chapters, more like a diary that tracked highlights during the author's time at the startup. The short "chapters" really made the book flow quickly.
I found the end a little hard to believe. It felt exaggerated but definitely made the ending more satisfying.
I also loved the structure of the book. No traditional chapters, more like a diary that tracked highlights during the author's time at the startup. The short "chapters" really made the book flow quickly.
I found the end a little hard to believe. It felt exaggerated but definitely made the ending more satisfying.
April 13, 2018
I found this book increasingly painful to read as it went on. I don't know if it is fiction (the copyright page claimed it as a work of fiction) or memoir or (most likely) a fictionalized memoir, but I could not understand why Lawrence put up with the degree of of bad management for so long. Maybe the technology was fun, but the situation was not.
February 3, 2021
Captivating
5 stars because the way Lawrence told the story was captivating. I learned many things about start-ups and several things about human behavior I had not considered before. I recommend this book to everyone. I wonder one thing - why were John’s emails and Slack messages so typo-filled and misspelled? No one called him out on it. Seems odd.
5 stars because the way Lawrence told the story was captivating. I learned many things about start-ups and several things about human behavior I had not considered before. I recommend this book to everyone. I wonder one thing - why were John’s emails and Slack messages so typo-filled and misspelled? No one called him out on it. Seems odd.
May 11, 2020
Very entertaining read, although the perspective feels a bit one-sided many times, and you have to ask yourself why some people (especially the author) reacted the way they did. Still, a good page-turner and a cautionary tale for anyone joining a young startup.
January 10, 2021
I found this book to be a better read than it has any right to be. My biggest complaint is that the cover holds it back. I’m not a programmer but worked at startups, small businesses, and Fortune 500 companies and so much of this rings true.
January 5, 2021
Very entertaining read. It brought out emotions of anxiety, frustration, absurdity and hilarity of being in a tech startup.
March 3, 2020
I loved the first 80% of it... which is enough to give a positive opinion I guess. What I didn't like really is that the book is written from the perspective of startup employee, not the founder. So there's only part of the story. Only information that the writer assumes. He uses a lot of exaggerations as well that are fun to read and enjoyable but some dialogues are hard to believe to be true.
I would recommend it to people working in tech startups... to feel good about the environment that they work for rather than take some valuable lesson from the book since it's more about management tyranny, mobbing and lack of transparency rather than actual reasons why startup failed from a perspective of a person that had full picture (instead of an employee).
I would recommend it to people working in tech startups... to feel good about the environment that they work for rather than take some valuable lesson from the book since it's more about management tyranny, mobbing and lack of transparency rather than actual reasons why startup failed from a perspective of a person that had full picture (instead of an employee).
May 3, 2021
Not sure what to think of this book. It's like watching sensationalized documentaries, informative but somehow you feel a lot of things are left out. Not a fan of the "glorification" of working crazy long hours and also the proud mention of the clickbait blog post titled "object oriented code is an expensive disaster which must end" really threw me off. Still it's a quick and fun read. A bit like reading the tabloids ¯\_(ツ)_/¯
July 7, 2021
A hilarious and page-turning romp through the world of tech-startups. Krubner's cast of characters are both disturbingly entertaining and eerily familiar - certainly for anyone with any experience as an entrepreneur or in the tech world. Shady VCs, dishonest business partners, overworked programmers at the mercy of demanding (and possibly delusional) CEOs, Krubner keeps the laughs and groans rolling in this easy, fun read.
April 17, 2022
Quick and entertaining, especially for anyone who’s worked in the software development side of a small startup.
This is a quick (I read it in an afternoon), entertaining read that will be appreciated the most by software developers who have worked for a small startup. Others will still enjoy it but will probably assume that it’s been exaggerated. As a software developer myself, I wish that were true!
This is a quick (I read it in an afternoon), entertaining read that will be appreciated the most by software developers who have worked for a small startup. Others will still enjoy it but will probably assume that it’s been exaggerated. As a software developer myself, I wish that were true!
June 11, 2023
Entertaining chronicle of a failed start-up
Thanks for pulling this together. It’s always helpful to learn from others. And this book is just that - an opportunity to learn from others. I especially appreciate your reference to lying and deceit … As I have personally experienced this unfortunate anti-pattern. The result was not pretty.
Thanks for pulling this together. It’s always helpful to learn from others. And this book is just that - an opportunity to learn from others. I especially appreciate your reference to lying and deceit … As I have personally experienced this unfortunate anti-pattern. The result was not pretty.
February 6, 2021
I wanted to like this book so much, but I couldn't help abandoning it around half time, even though its a thin one. There is no real twist or plot, its just downhill cringe, seasoned with the weird martyr / "I of course knew it" storytelling - sorry.
April 23, 2021
Terse and lightly ornamented, the book's unhurried tour through the inevitable collapse of a startup is strongest as a kind of counterexample in form and function to the trite parables that plague business books. A similarly succinct moral can be drawn, though: reality always wins in the end.
April 2, 2022
A good novel but I wouldn't take any reasons from it
A good novel but I wouldn't take any reasons from it. I think I would like more perspective on what happened in the view of the other characters.
A good novel but I wouldn't take any reasons from it. I think I would like more perspective on what happened in the view of the other characters.
December 31, 2017
A short, cautionary tale. Maybe Lawrence should have taken that corporate job!
January 29, 2023
Too much whining
Should have had the guts to tell Sital to get off youtube and focus - that’s leadership. By not quitting earlier, you are part of the reason management keeps on mistreating developers. I’m sure here are other startups you could have joined that had interesting tech to work on.
Should have had the guts to tell Sital to get off youtube and focus - that’s leadership. By not quitting earlier, you are part of the reason management keeps on mistreating developers. I’m sure here are other startups you could have joined that had interesting tech to work on.
June 14, 2025
Very funny!
Displaying 1 - 23 of 23 reviews